Hydrochloric Acid → 3-(2H-tetrazol-5-yl)-phenylamine hydrochloride

HRID 1588029Notes

Reaction equation

HRID 1588029 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[NH:14][N:13]=[N:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.[ClH:15]>C(O)C.[Pd]>[ClH:15].[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[NH:14][N:13]=[N:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 2851295-(3-nitrophenyl)tetrazole

Product 1

HCID 212019913-(2H-tetrazol-5-yl)-phenylamine hydrochlorideYield 71%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 5-(3-nitrophenyl)tetrazole (22 g, 0.12 mol) in ethanol (500 mL) was added 10% palladium on carbon (1.5 g, 7% (w /w)) in hydrochloric acid (23 mL of a 5M solution). The mixture was hydrogenated at 40 psi for 10 minutes then the catalyst filtered off and washed with water. The solvents were evaporated in vacuo and the brown solid azeotroped with toluene (4×100 mL). The resulting solid was triturated with hot ethanol to give 5-(3-aminophenyl)tetrazole hydrochloride (16.3 g, 71%) as a beige powder. mp 203°-205° C. 1H NMR (D2O) δ7.63 (1H, d, J=8 Hz), 7.75 (1H, dd, J=8 Hz), 8.00 (2H, m).

Workup

  1. filtrationthe catalyst filtered off
  2. washwashed with water
  3. customThe solvents were evaporated in vacuo
  4. customthe brown solid azeotroped with toluene (4×100 mL)
  5. customThe resulting solid was triturated with hot ethanol

Sources & evidence

ORD record
ord-e6e418ec12a8456bbf38a37bffe8f3c4
Source dataset
uspto-grants-1993_06
Patent number
US05220018

Reaction notes

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